2-Butanone, 3-bromo- → HCID 59497655, compound

HRID 1747435Notes

Reaction equation

HRID 1747435 reaction equation
[CH3:1][C:2]1[N:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH:13]([CH3:17])[C:14](=O)[CH3:15]>CC(C)=O>[CH3:7][O:6][C:4]([C:3]1[C:2]2[N:11]([C:13]([CH3:17])=[C:14]([CH3:15])[CH:1]=2)[CH:10]=[CH:9][CH:8]=1)=[O:5]

Participants

4

Reactant 2

HCID 131422-Butanone, 3-bromo-HCID 7015327Methyl 2-methylnicotinate

Product 1

HCID 59497655HCID 59497655, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methyl 2-methylnicotinate (4.9 g, 32.1 mmol) and 3-bromo-2-butanone (4.8 g, 32.1 mmol) in acetone (40 ml) were warmed to reflux for 3 d. Cooled to RT and partially purified the remaining residue via column chromatography (silica gel, 5-10% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give the desired product.

Workup

  1. temperatureto reflux for 3 d
  2. custompartially purified the remaining residue via column chromatography (silica gel, 5-10% EtOAc/hexanes)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ca2024298f454ac3a149384a82e56211
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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